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Graphene Nanoribbons Derived from Zigzag Edge-Encased Poly(para-2,9-dibenzo[bc,kl]coronenylene) Polymer Chains


Beyer, Doreen; Wang, Shiyong; Pignedoli, Carlo A; Melidonie, Jason; Yuan, Bingkai; Li, Can; Wilhelm, Jan; Ruffieux, Pascal; Berger, Reinhard; Müllen, Klaus; Fasel, Roman; Feng, Xinliang (2019). Graphene Nanoribbons Derived from Zigzag Edge-Encased Poly(para-2,9-dibenzo[bc,kl]coronenylene) Polymer Chains. Journal of the American Chemical Society, 141(7):2843-2846.

Abstract

In this work, we demonstrate the bottom-up on-surface synthesis of poly(para-dibenzo[bc,kl]-coronenylene) (PPDBC), a zigzag edge-encased analog of poly(para-phenylene) (PPP), and its lateral fusion into zigzag edge-extended graphene nanoribbons (zeeGNRs). Toward this end, we designed a dihalogenated di(meta-xylyl)anthracene monomer displaying strategic methyl groups at the substituted phenyl ring and investigated its applicability as precursor in the thermally induced surface-assisted polymerization and cyclodehydrogenation. The structure of the resulting zigzag edge-rich (70%) polymer PPDBC was unambiguously confirmed by scanning tunneling microscopy (STM) and non-contact atomic force microscopy (nc-AFM). Remarkably, by further thermal treatment at 450 °C two and three aligned PPDBC chains can be laterally fused into expanded zeeGNRs, with a ribbon width of nine (N = 9) up to 17 (N = 17) carbon atoms. Moreover, the resulting zeeGNRs exhibit a high ratio of zigzag (67%) vs armchair (25%) edge segments and feature electronic band gaps as low as 0.9 eV according to gaps quasiparticle calculations.

Abstract

In this work, we demonstrate the bottom-up on-surface synthesis of poly(para-dibenzo[bc,kl]-coronenylene) (PPDBC), a zigzag edge-encased analog of poly(para-phenylene) (PPP), and its lateral fusion into zigzag edge-extended graphene nanoribbons (zeeGNRs). Toward this end, we designed a dihalogenated di(meta-xylyl)anthracene monomer displaying strategic methyl groups at the substituted phenyl ring and investigated its applicability as precursor in the thermally induced surface-assisted polymerization and cyclodehydrogenation. The structure of the resulting zigzag edge-rich (70%) polymer PPDBC was unambiguously confirmed by scanning tunneling microscopy (STM) and non-contact atomic force microscopy (nc-AFM). Remarkably, by further thermal treatment at 450 °C two and three aligned PPDBC chains can be laterally fused into expanded zeeGNRs, with a ribbon width of nine (N = 9) up to 17 (N = 17) carbon atoms. Moreover, the resulting zeeGNRs exhibit a high ratio of zigzag (67%) vs armchair (25%) edge segments and feature electronic band gaps as low as 0.9 eV according to gaps quasiparticle calculations.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > Catalysis
Physical Sciences > General Chemistry
Life Sciences > Biochemistry
Physical Sciences > Colloid and Surface Chemistry
Uncontrolled Keywords:Colloid and Surface Chemistry, Biochemistry, General Chemistry, Catalysis
Language:English
Date:7 February 2019
Deposited On:22 Nov 2019 16:07
Last Modified:29 Jul 2020 11:50
Publisher:American Chemical Society (ACS)
ISSN:0002-7863
OA Status:Closed
Publisher DOI:https://doi.org/10.1021/jacs.8b10407
Project Information:
  • : FunderH2020
  • : Grant ID696656
  • : Project TitleGrapheneCore1 - Graphene-based disruptive technologies

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